I’m an advisor, speaker and author writing about the intersection of money and life. I’m not spouting untested philosophy—I work with clients and advisors as a Wealth Advisor and the Director of Personal Finance for Buckingham and the BAM Alliance, a community of investors and advisors who've discovered a better way to take control of financial futures and achieve life's most important goals. I’m thankful to have had my guidance vetted by one of the world’s best publishers through my book co-authored with Jim Stovall, "The Ultimate Financial Plan" (John Wiley & Sons). Most importantly, I’m living this stuff out in my foremost roles in life as a husband and father. A student of communication, I enjoy the practice in television (CNBC, ABC, CBS, NBC and Fox) radio (NPR) and print (featured in The Wall Street Journal, The New York Times, Kiplinger’s and Money magazines, among others).

Excessive Trading Leads To Death

Actually, the headlines on Friday, November 29th, 1940 read, “Livermore, Wall St. Wonder, Dead.”[i] I was recently re-acquainted with Jesse Livermore’s story—that of a self-made trading savant whose early-life exploits were regaled in a series of articles turned classic work of historical fiction, Reminiscences of a Stock Operator, by Edwin Lefevre[ii]. The volume is still handed out as a guide book to new traders every year, an ironic tradition considering the book was written as a cautionary tale.

It was first published in 1923, after Livermore had won and lost a couple fortunes already, but prior to his biggest take when he shorted the market in the Great Depression, increasing his net worth to a stunning $100 million. Livermore subsequently went bankrupt—not for the first time—and was suspended as a member of the Chicago Board of Trade in 1934. So why do we continue to romanticize the story of an investor who lost as much money as he ever made? Why do we glorify the existence of a man who, thrice married, deemed his life’s work an abject failure?

The story’s remarkable appeal should not surprise us—regardless of the futility of sustainable success in the business of gambling, the allure of the quick or easy fortune seems a siren’s song that will forever be sung, heard and followed. Maybe the appeal of Livermore’s sad story is that he did not follow his own rules, by his own admission, and that if we can manage to do so, we might be able to make the equivalent fortune without losing it.

Don’t bet on it. When attending to the business of fooling the market, we almost invariably end up fooling ourselves. And while one of the first stages of grief for the newly penniless may be blaming our failure on the market, like many others, Livermore eventually placed the blame where it rightly lay—on himself—and sadly took his own life at the age of 63.

Unfortunately, it’s not a stretch to suggest that dedicating ourselves wholly to the pursuit of money and riches often leads to death—literally for some but figuratively for many, many more. Relinquish the claim to overnight riches in favor of lifetime investing. You have a favorable probability of generating comfortable wealth through a lifetime of dedicated investing, but even the most disciplined gamblers eventually learn this sad truth—the house always wins.

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